Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1992-03-27
1995-01-17
Griffin, Ronald W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C07C40924, C08B 3700, A01N 3716, C11D 339, A61K 3119, A61K 700
Patent
active
053825713
DESCRIPTION:
BRIEF SUMMARY
It is an object of the invention to provide new derivatives of peroxyacids, their process of preparation and their uses.
It is known that peroxyacids are compounds which are difficult to handle. In crystallized state, they are indeed very often unstable. With respect to liquid peroxyacids, the fact that they are explosive, makes their purification difficult, and even impossible.
To solve the problem resulting from their unstability and in order to be able to make these compounds easily available, the inventors have studied the possibility of combining them with other molecules.
These operations have led them to study and develop a new series of compounds.
Therefore the aim of the invention is to provide new derivatives of peroxyacids in a form which is stable for a long period of storage, enabling to provide peroxyacids which are easily available when they have to be used.
The invention also aims at a process for obtaining these derivatives which is easy to carry out, as well as their application, in particular in the field of disinfection, bleaching and organic synthesis.
The new derivatives of peroxyacids of the invention are characterized in that they are inclusion compounds, or clathrates, in a hollow molecule which is capable of behaving as a receiving structure with respect to a given peroxyacid.
The association between the peroxyacids and the host molecule is essentially based on the plurality of Van der Waals bonds between the two compounds. Already when the clathrate is placed in solution or upon heating, the inserted substance is released and is therefore available for use.
The molecules which are used as receiving structure are selected among compounds which, under the conditions used for their preparation, are inert with respect to peroxyacids, provide a hydrophobic cavity of suitable shape and dimensions which is capable of containing at least one molecule of peroxyacid, and holding within its cavity the molecule(s) of peroxyacid.
In a general manner, host molecules of this type comprise for example cavitands as suggested by Peterson in Science News, vol. 132, 90-93, 1987 and Milgrom in New Scientist, 61-64, 1988, or cyclophanes (see chapter 11, p. 629 and following, of Odashima et al in Academic Press, 1983, edited by P.M. Keehn and S. M. Rosenfeld).
According to a preferred embodiment of the invention, the receiving molecule has the structure of a cyclodextrin.
It is known that the cyclodextrins (CD) are cyclic oligoglucosides obtained by enzymatic degradation of starch. They are represented by the formula (C.sub.6 H.sub.10 O.sub.5).sub.n.
Inclusion derivatives in cyclodextrins have already been described (see Cyclodextrins and their Inclusion Complexes of J. Szejtli, Akademiai kiado, Budapest, 1982).
Among these derivatives, the inclusion of organic acids and of certain organic hydroxyperoxides has been considered essentially with a view to improve their heat stability and to decrease their vapor tension.
However, the same techniques which were applied to the microencapsulation of H.sub.2 O.sub.2 have not permitted to isolate crystallized clathrates.
It was therefore completely unexpected to include according to the invention a peroxyacid in a receiving structure of the cyclodextrin type.
Cyclodextrins especially suitable according to the invention comprise alpha-cyclodextrin (or cyclohexamylose), beta-cyclodextrin (or cycloheptamylose) or gamma-cyclodextrin (or cyclooctamylose).
The cyclodextrins used are possibly substituted when it is intended to give them specific properties. By way of example, substitutions with alkyl, maltosyl or hydroxypropyl groups and those described in the article of J. Szejtli, previously mentioned, will be mentioned.
Bearing in mind the process of preparation used, cyclodextrins are more generally hydrated. This residual water content has an advantageous effect on preservation, by promoting a slow escape of the peroxyacid in the humidity of the air.
The diameter of the cavity is from 5 to 6 Angstroms for alpha-cyclodextrin and its depth is of 7 to 8 Angstroms.
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"Stabilization of Hydroperoxides by Means of the Formaion of Inclusion Compounds with .beta.-Cyclodextrin", Matsui et al., Bulletin of the Chemical Society of Japan, vol. 43, No. 6, p. 1910.
Kurozumi et al., "Inclusion Compounds of Non-Steroidal Antiinflammatory and Other Slightly Water Soluble Drugs with .alpha.-and .beta.-Cyclodextrins in Powdered Form", Chem. Pharm. Bull., vol. 23 (No. 12) pp. 3062-3068 (1975).
DuPont Michel
Granger Michel
Ledon Henry
Chemoxal S.A.
Griffin Ronald W.
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